AR Strategy & AI Deployment Lead

Monk; New York (NY); On-site; USD 150,000 - 210,000; Full time

Benefits offered by this job

Equity

Medical coverage

Dinner stipend

Flatiron office

Job summary

Monk is an AI-native accounts receivable platform helping B2B companies get paid faster. We are building an AI-powered AR stack and partnering with Customer finance teams to deploy bespoke solutions that improve cash flow.

This role leads deployment, customer outcomes, and on-site product demonstrations to drive measurable KPI improvements. You will own the AR strategy with customers, map workflows, and collaborate with Engineering to influence the product roadmap, while maintaining strong

Qualifications

• 4+ years at a top-tier management consultancy or investment bank, or a comparable high-ownership operating role.
• Exceptional communication and executive presence. You can hold the room with a CFO, CEO, and Head of Accounting.
• Stellar presentation skills, including demos, slides, memos and on the spot whiteboard presentations.
• Strong analytical and structured problem-solving instincts. You break ambiguous problems into solvable pieces and drive them to a number.
• High agency and resilience. You own the outcome, manage scope, and do whatever it takes to make our Customers win.
• Comfort getting hands‑on with software and non‑deterministic systems. You don’t need to be an engineer, but you need to be unafraid to build, configure, and iterate.
• Bias to action

Responsibilities

• Act as a strategic advisor to CFOs, controllers, and AR leaders. Drive their AR strategy and make the value explicit in their language.
• Own the full deployment lifecycle for a book of Customers, from scoping through go-live through ongoing optimization and expansion.
• Establish yourself as a trusted advisor and expert in deploying AI to solve revenue-related challenges.
• Go on-site and lead custom product demonstrations and working sessions.
• Map each Customer’s AR process in detail (collections, cash app, disputes, vendor portals, edge cases) and translate it into agent workflows, escalation policies, and playbooks.
• Own the Customer’s KPIs and report against them. Surface expansion and drive renewals off demonstrated outcomes.
• Be the Customer’s voice internally. Feed insights back to Engineering to shape the product roadmap.

Skills

Strategic adviser

Executive presence

Presentations

Analytical thinking

Ownership

Hands-on with software

Bias to action

Job description

Monk is an AI-native accounts receivable platform helping B2B companies get paid faster. We are building an AI-powered AR stack and partnering with Customer finance teams to deploy bespoke solutions that improve cash flow.

This role leads deployment, customer outcomes, and on-site product demonstrations to drive measurable KPI improvements. You will own the AR strategy with customers, map workflows, and collaborate with Engineering to influence the product roadmap, while maintaining strong